That Awkward Moment You Have To Spend Lots Of Money…

I’ve had two scenarios over the past year where one of my electronic devices crapped the bed (like, where did that phrase even come from?) Both times it cost me a lot of money. Both times….I lived regardless.

Scenario #1: My phone stopped working. 

It was the day after my girlfriend and I broke up. (As if things weren’t bad enough.) My phone suddenly wouldn’t stay on for more than a few second before flickering off. So I brought it to Verizon and learned some bad news: I needed a new phone. Like, yesterday.

That was the bad news. Here was the good news: I now had an excuse to get an iphone. I love it. It’s far better than any phone I had before. I also got a free bluetooth speaker and started listening to self help books and podcasts while I biked. (And I bike a lot.) 

So a bunch of good things came from this really, really inconvenient situation.

As for the money? I put it on a credit card. Yes I’m still paying it off. But fast forward eight months and I’m so much closer to paying it off, thanks to free financial coaching at Next Door Chicago.


Scenario #2: I spilled water on my laptop. 

Friends…don’t do this. It’s a very, very expensive spill.

I went without a laptop for a bit. And I live on my laptop.

What I did instead? I used my phone and tablet. Not perfect, but it got the job done. OH, and I got it back IN TWO DAYS. It was expensive, but it was back as good as new in just two days….also, I didn’t lose any of my information. #win

And the money? It came out of my savings. Because I’m trying this thing where I don’t put more money on my credit card. (We’ll see how it goes…)


Here’s the point: There’s going to be situations where we lose something valuable or have to spend a lot of money. Or both. (Ugh.) And you’re going to be okay. You’re not dead. You’ll adjust and still move on. Parts of it will suck. But you’ll still be awesome.

Don’t let external events define you. You’re #notperfect. But you’re #stillenough.

Go get ’em, friend.


Some cool Chicagoans decided to make a sign saying LOVE for everyone commuting on Lake Shore Drive recently! 

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Have you checked out the Tony Rossi Show podcast yet? (I heard it’s good…) 

By the way, I’m Tony. I live in Chicago. (Duh.) I’m an actor and podcaster living right up the street from Wrigley Field. 

My blog is here to help others take control and live a more authentically positive life on their terms. Since working with a coach and learning more about personal development, I’ve started sharing my learnings with others. (I have a lot…)

If we’ve never meet – shoot me a tweet!  Would love to hear how you found this 🙂You can also find me on facebook, instagramYouTube, or check out my actor website

Oh – and I’m now on iTunes! #TonyRossiShow


Your Artistic Struggle Doesn’t Have to Suck

What’s up my friends?! 

This post was originally written for Which you know because you already follow my posts there….right? (RIGHT?!) 

Sorry. Read on. 

It was a rainy Tuesday afternoon and I couldn’t wait: in a few hours, I’d be attending my first-ever opening night performance and after party with one of my favorite big Chicago theaters. Mind you, I hadn’t purchased the tickets—yours truly is in credit card debt and waiting to book that national commercial. These were comps. If they weren’t, I wouldn’t be going to this premiere event.

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It was kind of good. 

Speaking of finances, I knew I had to check my accounts and go over a few things before I left for the evening. This absolutely was not my favorite part of the day (see above), but it was necessary. And that day, it was extra necessary.

You see, I had made a grave error while attempting to make a small credit card payment the night before. Instead of making a small one, I made a very large payment, accidentally paying off the entire thing. I quickly called my credit card company but they couldn’t do anything because the payment was still “processing.” So I called my bank and got the “We’re experiencing a higher volume than usual” message before waiting on hold.

To add insult to injury: I had to message my acting coach about the check that she wouldn’t be able to cash because of my mistake. Why did I hire a coach? Because I had recently auditioned to attend the School at Steppenwolf, a move that would cost another several thousand dollars.

So here I was with a negative bank account, credit card debt, waiting to let my acting coach know if and when she could get her money, and wringing my hands over whether I’d get accepted to the school. Needless to say, it was not a relaxing day. Luckily, I had a trick, one I learned from thought leader and author, Preston Smiles: ask empowering questions.


I stole this photo – with love, (duh), from Preston’s Smiles Facebook page. He credits @jennaphillipsballard with the photo. That’s all. Carry on! 

During challenging situations like this, we can ask, “Will this matter three years from now? What good is here that I currently cannot see?”

I didn’t know how this issue would be resolved. But no, it wouldn’t matter three years from now. And the good here is that I can tell this story to inspire others who will realize I didn’t just make it big overnight and with ease. This takes work. This takes nerves. This takes mistakes and over-drafted bank accounts and bounced checks.

So what’s your challenge? Finances? A broken heart? Frustration with the industry? Will any of it matter three years from now? (Hint: Probably not.)

Let me know. Let all of us know. There might not be any evidence of your triumph yet but believe in yourself now anyway. And then when you’ve made it to the top, shout it to the rooftops.

You deserve to feel amazing exactly where you are today.

Let’s go get ’em, friends.

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What’s that? You want to hire me for coaching?!

Or maybe give an empowerment talk to your group or school?

Email me! Let me know how I can help.

Same goes for questions – you can ask those for free 😉 

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Thanks for reading!

By the way, I’m Tony. I live in Chicago. (Duh.) I’m an actor and blogger living right up the street from Wrigley Field. 

My blog is here to help others take control and live a more authentically positive life on their terms. Since working with a coach and learning more about personal development, I’ve started sharing my learnings with others. (I have a lot…)

If we’ve never meet – shoot me a tweet!  Would love to hear how you found this 🙂You can also find me on facebook, instagramYouTube, or check out my actor website

BIG NEWS! (And a post….I promise…)

Hey TonyinChicago readers!

For those of you who have hit that “subscribe” button below – many thanks 🙂 I love seeing that others are resonating with the idea of being a more authentically happy person.

Because I want to spread the word of how much control we have over our own happiness, I’ve started applying to other websites.

(Fear not – TonyinChicago isn’t going anywhere 😉 )

In the meantime, I’ve started contributing to a new website called One of my favorite posts just got uploaded and I’m happy to share with you all today….

“The Journey To Happiness”

(This one’s for you, actors with day jobs!)

When I first got to Chicago, I wanted a job. Any job. I had moved to pursue acting, but I couldn’t be an actor without money. So I applied anywhere and everywhere.

My first gig was at a toy store. I made $8.50 an hour. The staff and customers were kind, but the job didn’t excite me. Between the pay and my desire to do a bit more exciting work, I needed a change.

I got an office job. I was a receptionist. (I know. Not very exciting.) I made $9.00 an hour and worked 40 hours a week. With a few exceptions, both the staff and the clients here were not too kind and caring….I very much needed a change.


Click here to read the full post! 

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Tony is a theatre and film actor living in Chicago, just up the street from Wrigley Field 🙂 He loves helping others to become the happiest version of themselves so that they can live more fun, fulfilled lives on their own terms.

He also loves to blog on how to do this. 

Contact him for a free one-on-one to see if he can help you with your own mindset and happiness in life, or to inquire if he can do some writing for you!  You can reach him at

PS – Rumor has it that he loves when you hit that “share” button for friends and family to see 😉 

Had You Won The Power Ball, You Still Wouldn’t Be Happy

If you do non union extra work in Chicago, you might have heard the Rosemont story:

A group of us booked a job through 4 Star Casting (who are amazing, by the way). All we knew was that we’d be standing in line outside a convention center in Rosemont. After a long day of confusion, we got some cash for literally holding spots in line for collectors at a coin show. And it didn’t end there: We got the chance to return and hold more spots in line.

For more cash. (A lot more.)

This time, we’d need a good spot. A spot to get in early enough that we’d enter the show before the rest of the crowd.  If we got in, we’d get our hands on an item that was woth a lot of money.

And there were plenty of others who knew about it.

The next few days were hectic: Texts throughout the night, sleeping outside, getting soaked by sprinklers…you name it. Oh, and there were stampedes to get in line, threats to anyone who was cutting or holding a spot, and lots of other fun stories. It got bad enough that the final day of the coin show was cancelled due to safety concerns.

Money can do a lot. And there’s a lot of misconception behind it.


What doesn’t make you happy

Marcus Persson is a billionaire. Known as the creator of Minecraft, he made himself quite a fortune. Last August, Persson sent out a series of tweets sharing how he was lonely, unhappy and afraid to pursue future success.

Andre Agassi is a tennis pro. He won eight Grand Slams and an Olympic gold medal. In less than a day after becoming number one in the world, he was roaming the streets, wondering why he felt so empty. He later was tested positive for crystal meth.

Money and fame isn’t what makes us happy.


What does make you happy

In my experience, the truly happy people in the world are the ones who went through a struggle. Rather than allow their dreams to suffer, they learned from the struggle and grew. Along the way, they grew even more and appreciated life better because of  it.

I’m not saying we all need to suffer in order to be happy. I am saying that struggles help us learn how we want to feel to truly find happiness.

I’ll use myself as an example: If I had more money, I’d be working fewer jobs I don’t want to go to. We’re talking, I can’t fall asleep because going to this job makes me so unhappy.

If I had more money, it would mean more time working jobs that are creative, fulfilling, and meaningful. It would mean more time creating experiences. Money would allow me to visit the Boston area. I’d see my parents, grandparents, and cousins more often.  I’d see my college and highs school friends that I only see once or twice a year (if that).

It would mean more time to pursue creative jobs onstage, behind the camera, and across the country motivating students to live their crazy, awesome life.

I want more experiences with others. I want more opportunities to add value to others though art and motivation.

Yes, a lottery ticket would help fund those dreams. But a paycheck from my agent that sends me to Boston for a commercial – that’s more special than anything I could get from 711. (Don’t get me wrong, grateful they were open late so I could buy cheese on New Year’s).

How do you want to feel? Base your goals off that. Then go after it. Seriously. There are too many experiences and people you care about waiting for you to put this off anymore.

Go get ‘em.


Did you like this post? Oh good. I hoped you would. I write this blog for free so that others can get insights that they wouldn’t have otherwise gotten. I’d love for you to share on social media with others who might benefit too 🙂